Ultimate Sissy Weekend Stories

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Discovering Mistress Sarah's World Pt. 08

by oneguy4fun on Sep 14, 2017
Transsexuals & Crossdressers

Part 8 -- Complete Surrender Chapter 21 Leaving Behind Joe's Life Mistress Sarah was very pleased with Josie's training and feminization. She was anxious to have complete reign over him so she sent him home a day early to pack up his things and prepare to leave behind his life in the Philadelphia suburbs. "I'm sending May with you Josie," announced Mistr...

Sissy's New Toy Ch. 02

by sissyfemme on Sep 16, 2017
Fetish

"Oh, and what might that be?" I asked coyly. Her hand fished around again under the pillow and came out with a bottle of Astro-Glide. She unsnapped the top with a flourish and began to drizzle it down her shaft, working it in and around with her free hand. She used lots so her cock was shining and her fingers were still covered in the stuff. "Pull down your...

Young Master Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a ch...

Who I Am Ch. 05

by AngelSand on Sep 13, 2017
Novels and Novellas

New Readers: Thank you for checking me out! Each chapter builds from the previous. I highly suggest you start from chapter 1. Returning Readers: Thank you so much as always. I appreciate every email and comment. I hope you continue to read my stuff!! Please excuse any typos. I am self-editing. Ms. Angel Sand All copyrights reserved. No part of this docu...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

I Learned My Lesson Well Ch. 02

by Angelscuck on Sep 14, 2017
Transsexuals & Crossdressers

As I told you in part 1, Angel really taught me a lesson regarding cumming without her permission. I was so grateful that I hadn't lost her to a superior black stud, I was even afraid to masturbate to porn on the internet. We have two computers, hers and mine, next to each other in our office. She told me she had forwarded an email to me from one of her gi...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...

A Birthday to Remember! Ch. 05

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Decidedly put in my sissy submissive place by Mistress Leader Marta, I resolved to be much more careful and obedient. I also was aware of my excitement at her Dominance and power. When another participant sat down next to me, I was recovered enough to look up to say hello. I recognized him as one of those I had seen earlier standing around and chatting afte...